Although oral nicotine replacement therapies (NRTs) have been found effective in improving quit rates of smokers, poor compliance, among other factors, has led to less than optimal efficacy in typical use conditions. Therefore, the purpose of this project is to develop and test the feasibility of an integrated web and wireless text messaging or SMS application to provide prompted dosing of NRTs in real time based on the user's smoking patterns and preferences (e.g. smoking rates, dependence, quit date, type of NRT to be used). The prototype program will allow users to set up and personalize the dosing schedule based on a brief assessment on the web. The web application also will provide the user with behavioral adjuncts and social support mechanisms. The text messaging component will prompt each dose on the user's cell phone text messaging system and will also provide behavioral tips and relapse prevention coping strategies as appropriate. The system also will be interactive, allowing the user, either from the web or the text messaging component, to adjust the schedule based on cravings or side effects experienced. Once developed and tested, the NRT Text Messaging program will be evaluated in a small randomized controlled trial of 125 nicotine gum users comparing the NRT text messaging program to a generic, unscheduled text messaging condition. Subjects will be assessed on gum use, smoking rate, quit status, dependence, and withdrawal at baseline and 8 weeks post quit date. Phone assessments at week 1 and 4 post-quit date also will be performed. Significant differences in nicotine gum use as well as positive subjective ratings of usability will be primary feasibility criteria for this trial.